The Biggest Dating Disaster Stories

The Biggest Dating Disaster Stories

It’s a skill, really. Some women play jazz flute. Some make fine Italian cuisine. But my special talent, it seems, is going on bad dates. I’ve been out with an athlete who bragged about groupies polishing his toenails; a finance guy who casually mentioned that he was under federal investigation; and a blogger who danced like a drunken baby.

Then there was John.* I was elated when this cute, shy events planner got my number from a mutual friend and asked me out to dinner. On date night, I—a flats-and-jeans girl—slipped on red four-inch heels and a pencil skirt. I even got to the restaurant early. Forty-five minutes and six “I’m so sorry” texts later, John arrived. Dinner actually went well—until an elderly hippie wearing a sarong slid into our booth, greeted us in Swahili and bought marijuana from John right in front of me.

Of course, there is one good thing about having so many truly horrific dates: getting to rehash all of the gory details with other lucky ladies. Therefore, I present some of the most awkward, most bizarre, most awesomely bad dates in the history of womankind—for official confirmation that, really, it’s not us; it’s them.

Photo: iStock

“When the movie my date wanted to see was sold out, we went to my first choice instead. A few minutes into the film, he announced he was going to get us some candy. Twenty minutes passed. Then 30. Worried, I sent him a text. No response. I even checked the lobby. An hour later, as the credits rolled, this fool came strolling into my theater bragging about how he’d snuck in to see the movie he’d wanted!” —Chauncie Burton, 28, Chicago

“My girlfriend and I met two guys at a lounge and liked them enough to move to their table. Three hours later, after lots of dancing and flirting, the police showed up. Seems our dates had been buying us drinks with stolen credit cards the entire time!” —Rochelle Spencer, 32, Augusta, Ga.

“For our first date, Eric* said we were going out for a ‘nice meal.’ I was shocked when we arrived at his parents’ just in time for Sunday dinner. I hardly knew him, so it was incredibly awkward. Even worse, his grandmom kept asking how many children I was willing to have!” —Chinwe Etoh, 24, Baltimore

Photo: iStock

“Once on a movie date, the guy waited until we got to the ticket window of the theater to tell me we were going dutch. OK, sure. After the film, he wanted to go to the Arby’s drive-through so we could grab something to eat. Before he put in the order, he turned to me and hissed, ‘You’re paying for yours!’ and for about five minutes grumbled to himself about ‘greedy women with their hands out.’ Obviously we didn’t see each other again.” —Tarana Burke, 36, Philadelphia

“This guy took my meat-eating Texan ass to a raw food, vegan restaurant. For an entire hour—I am not exaggerating—he explained to me, in the most vivid detail, how cow’s milk was actually pus. Clearly this wasn’t a love connection.” —Renee Good, 38, Prairie View, Tex.

“I went to dinner with an older man who happened to make considerably more money than I did. Regardless, when the check arrived, he quickly did the calculations and split it in half. No problem, but then he told me, ‘Oh, actually you owe me another dollar—you ordered the white meat.’” —Zuhirah Khaldun, 33, East Elmhurst, N.Y.

“In college I went out with a guy the night before summer vacation. After dinner I told him I needed to get home because my flight was really early. To prolong our time together, he drove 20 miles an hour the whole way. He wasn’t bothered at all by the honks, middle fingers and shouts from the other drivers who swerved around us. He even told me I was wrong to ask him to speed up, because I should appreciate how romantic he was.” —Adia Harvey Wingfield, 32, Raleigh, N.C.

“On a hiring panel for my company, I met a really attractive interviewee. Although he didn’t get the position, he did call to ask me to go to dinner. We had a great time, so imagine my surprise when I arrived for our second date and saw him standing at the bar talking to another woman. He gave me a big hug and said, ‘There’s someone I want you to meet—my fiancee. I’ve told her all about you!’”—Tenecia Harris, 27, New York City

“My twin and I had dinner with two gorgeous brothers who calmly said they were aliens who’d come to Earth to find wives!”—Hillary Garcia, 40, Macon, Ga.